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Piperlongumine

Piperlongumine

Product ID P3561
Cas No. 20069-09-4
Purity ≥98%
Product Unit SizeCostQuantityStock
25 mg $77.70 In stock
100 mg $245.30 In stock
250 mg $510.50 In stock
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  • Description
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Description

Piperlongumine is found in several species of the Piper plant and displays many beneficial characteristics, including antithrombotic, anti-inflammatory, anti-atherosclerotic, and chemotherapeutic activities. Piperlongumine directly inhibits thromboxane A2 (TxA2) receptors, inhibiting platelet aggregation in vivo. Piperlongumine also decreases NF-κB activation and inhibits PDGFR signaling in vivo, inhibiting cell migration and decreasing atherosclerotic plaque formation. In a cellular model of prostate cancer, piperlongumine inhibits NF-κB activity and decreases expression of IL-6, IL-8, MMP9, and ICAM-1, decreasing cell invasion and growth; in a separate study using a similar model, this compound prevents transcription of androgen receptors, decreasing androgen receptor protein levels. In several other cellular models of cancer (including glioblastoma multiforme and colon cancer), piperlongumine inhibits the ubiquitin-proteasome system, likely at a pre-proteasomal stage, increasing reactive oxygen species (ROS) and stimulating activation of p38, resulting in autophagy and cell death. It is a novel CRM1 inhibitor.

Product Info

Cas No.

20069-09-4

Purity

≥98%

Formula

C17H19NO5

Formula Wt.

317.34

Chemical Name

(E)-1-(3-(3,4,5-Trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one

IUPAC Name

1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one

Synonym

1-[(2E)-3,4,5-trimethoxyphenyl)prop-2-enoyl]-5,6-dihydropyridin-2-(1H)-one, Piplartine

Solubility

DMSO (~25 mg/ml)

Appearance

Yellow Powder

Shipping and Storage

Store Temp

-20°C

Ship Temp

Ambient

Downloads

MSDS

P3561 MSDS PDF

Info Sheet

P3561 Info Sheet PDF

References

Ginzburg S, Golovine KV, Makhov PB, et al. Piperlongumine inhibits NF-κB activity and attenuates aggressive growth characteristics of prostate cancer cells. Prostate. 2013 Oct 22. [Epub ahead of print]. PMID: 24151226.

Wang Y, Wang JW, Xiao X, et al. Piperlongumine induces autophagy by targeting p38 signaling. Cell Death Dis. 2013 Oct 3;4:e824. PMID: 24091667.

Liu JM, Pan F, Li L, et al. Piperlongumine selectively kills glioblastoma multiforme cells via reactive oxygen species accumulation dependent JNK and p38 activation. Biochem Biophys Res Commun. 2013 Jul 19;437(1):87-93. PMID: 23796709.

Jarvius M, Fryknäs M, D'Arcy P, et al. Piperlongumine induces inhibition of the ubiquitin-proteasome system in cancer cells. Biochem Biophys Res Commun. 2013 Feb 8;431(2):117-23. PMID: 23318177.

Son DJ, Kim SY, Han SS, et al. Piperlongumine inhibits atherosclerotic plaque formation and vascular smooth muscle cell proliferation by suppressing PDGF receptor signaling. Biochem Biophys Res Commun. 2012 Oct 19;427(2):349-54. PMID: 22995306.

Golovine KV, Makhov PB, Teper E, et al. Piperlongumine induces rapid depletion of the androgen receptor in human prostate cancer cells. Prostate. 2013 Jan;73(1):23-30. PMID: 22592999.

Iwashita M, Oka N, Ohkubo S, et al. Piperlongumine, a constituent of Piper longum L., inhibits rabbit platelet aggregation as a thromboxane A(2) receptor antagonist. Eur J Pharmacol. 2007 Sep 10;570(1-3):38-42. PMID: 17618620.

Niu M, Xu X, Shen Y, Yao Y et al., Piperlongumine is a novel nuclear export inhibitor with potent anticancer activity. Chem Biol Interact. 2015 Jul 25;237:66-72. PMID: 26026911 DOI: 10.1016/j.cbi.2015.05.016.

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